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Copyright © 2015 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 2e Chapter 13 Alcohols and Phenols Organic Chemistry Second Edition.

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Presentation on theme: "Copyright © 2015 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 2e Chapter 13 Alcohols and Phenols Organic Chemistry Second Edition."— Presentation transcript:

1 Copyright © 2015 John Wiley & Sons, Inc. All rights reserved. Klein, Organic Chemistry 2e Chapter 13 Alcohols and Phenols Organic Chemistry Second Edition David Klein

2 13.1 Alcohols and Phenols Alcohols possess a hydroxyl group (-OH) Hydroxyl groups are extremely common in natural compounds Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

3 13.1 Alcohols and Phenols Hydroxyl groups in natural compounds Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

4 Phenols possess a hydroxyl group directly attached to an aromatic ring 13.1 Alcohols and Phenols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

5 13.1 Alcohols Nomenclature Alcohols are named using the same procedure we used in Chapter 4 to name alkanes with minor modifications 1.Identify the parent chain, which should include the carbon that the –OH is attached to 2.Identify and Name the substituents 3.Assign a locant (and prefix if necessary) to each substituent. Give the carbon that the –OH is attached to the lowest number possible 4.List the numbered substituents before the parent name in alphabetical order. Ignore prefixes (except iso) when ordering alphabetically 5.The –OH locant is placed either just before the parent name or just before the -ol suffix Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

6 13.1 Alcohols Nomenclature Alcohols are named using the same procedure we used in Chapter 4 to name alkanes with minor modifications 1.Identify the parent chain Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

7 13.1 Alcohols Nomenclature Alcohols are named using the same procedure we used in Chapter 4 to name alkanes with minor modifications 3.Assign a locant (and prefix if necessary) to each substituent. Give the carbon that the –OH is attached to the lowest number possible taking precedence over C=C double bonds Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

8 13.1 Alcohols Nomenclature Alcohols are named using the same procedure we used in Chapter 4 to name alkanes with minor modifications 5.The –OH locant is placed either just before the parent name or just before the -ol suffix R or S configurations should be shown at the beginning of the name Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

9 13.1 Alcohols Nomenclature For cyclic alcohols, the –OH group should be on carbon 1, so often the locant is assumed and omitted Common names for some alcohols are also frequently used Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

10 13.1 Alcohols Nomenclature Like halides, alcohols are often classified by the type of carbon they are attached to WHY do we use these classifications? Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

11 13.1 Alcohols Nomenclature When an –OH group is attached to a benzene ring, the parent name is phenol Practice with SkillBuilder 13.1 Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

12 13.1 Alcohols Nomenclature Name the following molecule Draw the most stable chair conformation for (cis)-1- isopropyl-1,2-cyclohexanediol Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

13 13.1 Commercially Important Alcohols Methanol (CH 3 OH) is the simplest alcohol With a suitable catalyst, about 2 billion gallons of methanol is made industrially from CO 2 and H 2 every year Methanol is poisonous, but it has many uses 1.Solvent 2.Precursor for chemical syntheses 3.Fuel Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

14 13.1 Commercially Important Alcohols Ethanol (CH 3 CH 2 OH) has been produced by fermentation for thousands of years. HOW? About 5 billion gallons of ethanol is made industrially from the acid-catalyzed hydration of ethylene every year Ethanol has many uses 1.Solvent, precursor for chemical syntheses, fuel 2.Human consumption – ethanol suitable for drinking is heavily taxed. Ethanol used for purposes other than drinking is often denatured. WHY? Is it poisonous? Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

15 13.1 Commercially Important Alcohols Isopropanol is rubbing alcohol. Draw its structure Isopropanol is made industrially from the acid-catalyzed hydration of propylene Isopropanol is poisonous, but it has many uses 1.Industrial solvent 2.Antiseptic 3.Gasoline additive Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

16 13.1 Physical Properties of Alcohols The –OH of an alcohol can have a big effect on its physical properties Compare the boiling points below Explain the differences Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

17 Because they can H-bond, hydroxyl groups can attract water molecules strongly Alcohols with small carbon chains are miscible in water (they mix in any ratio). WHY? Alcohols with large carbon chains do not readily mix with water 13.1 Physical Properties of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

18 Do hydrophobic groups repel or attract water? WHY are molecules with large hydrophobic groups generally insoluble in water? Alcohols with 3 or less carbons are generally water miscible Alcohols with more than 3 carbons are not miscible, and their solubility decreases as the size of the hydrophobic group increases 13.1 Physical Properties of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

19 An alcohol’s potency as an anti-bacterial agent depends on the size of the hydrophobic group 13.1 Physical Properties of Alcohols To kill a bacterium, the alcohol should have some water solubility. WHY? To kill a bacterium, the alcohol should have a significant hydrophobic region. WHY? Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

20 Hexylresorcinol is used as an antibacterial and as an antifungal agent It has a good combination of hydrophobic and hydrophilic regions – It has significant water solubility – Its nonpolar region helps it to pass through cell membranes Practice with conceptual checkpoint Physical Properties of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

21 A strong base is usually necessary to deprotonate an alcohol A preferred choice to create an alkoxide is to treat the alcohol with Na, K, or Li metal. Show the mechanism for such a reaction Practice with conceptual checkpoint Acidity of Alcohols and Phenols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

22 Recall from chapter 3 how ARIO is used to qualitatively assess the strength of an acid Lets apply these factors to alcohols and phenols – Atom 13.2 Acidity of Alcohols and Phenols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

23 Lets apply these factors to alcohols and phenols – Resonance – Explain why phenol is 100 million times more acidic than cyclohexanol – Show all relevant resonance contributors 13.2 Acidity of Alcohols and Phenols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

24 Given the relatively low pK a of phenols, will NaOH be a strong enough base to deprotonate a phenol? 13.2 Acidity of Alcohols and Phenols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

25 Lets apply these factors to alcohols and phenols – Induction: unless there is an electronegative group nearby, induction won’t be very significant – Orbital: in what type of orbital do the alkoxide electrons reside? How does that effect acidity? 13.2 Acidity of Alcohols and Phenols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

26 Solvation is also an important factor that affects acidity Water is generally used as the solvent when measuring pK a values Which of the alcohols below is stronger? ARIO cannot be used to explain the difference 13.2 Acidity of Alcohols and Phenols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

27 Solvation explains the difference in acidity Draw partial charges on the solvent molecules to show how solvation is a stabilizing effect Practice with SkillBuilder Acidity of Alcohols and Phenols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

28 Use ARIO and solvation to rank the following molecules in order of increasing pK a 13.2 Acidity of Alcohols and Phenols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

29 We saw in chapter 7 that substitution reactions can yield an alcohol What reagents did we use to accomplish this transformation? We saw that the substitution can occur by S N 1 or S N Preparation of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

30 The S N 1 process generally uses a weak nucleophile (H 2 O), which makes the process relatively slow Why isn’t a stronger nucleophile (-OH) used under S N 1 conditions? 13.3 Preparation of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

31 In chapter 9, we learned how to make alcohols from alkenes Recall that acid-catalyzed hydration proceeds through a carbocation intermediate that can possibly rearrange How do you avoid rearrangements? Practice with checkpoints 13.7 and Preparation of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

32 A third method to prepare alcohols is by the reduction of a carbonyl. What is a carbonyl? Reductions involve a change in oxidation state Oxidation state are a method of electron bookkeeping Recall how we used formal charge as a method of electron bookkeeping – Each atom is assigned half of the electrons it is sharing with another atom – What is the formal charge on carbon in methanol? 13.4 Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

33 For oxidation states, we imagine the bonds breaking heterolytically, and the electrons go to the more electronegative atom 13.4 Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

34 Each of the carbons below have zero formal charge, but they have different oxidation states Calculate the oxidation number for each Is the conversion from formic acid  carbon dioxide an oxidation or a reduction? What about formaldehyde  methanol? Practice with SkillBuilder Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

35 The reduction of a carbonyl requires a reducing agent Is the reducing agent oxidized or reduced? If you were to design a reducing agent, what element(s) would be necessary? Would an acid such as HCl be an appropriate reducing agent? WHY or WHY NOT? 13.4 Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

36 There are three reducing agents you should know 1.We have already seen how catalyzed hydrogenation can reduce alkenes. It can also work for carbonyls – Forceful conditions (high temperature and/or high pressure) 13.4 Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

37 Reagents that can donate a hydride are generally good reducing agents 2.Sodium borohydride 13.4 Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

38 Reagents that can donate a hydride are generally good reducing agents 3.Lithium aluminum hydride (LAH) 13.4 Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

39 Note that LAH is significantly more reactive that NaBH 4 LAH reacts violently with water. WHY? How can LAH be used with water if it reacts with water? 13.4 Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

40 Hydride delivery agents will somewhat selectively reduce carbonyl compounds 13.4 Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

41 The reactivity of hydride delivery agents can be fine- tuned by using derivatives with varying R-groups – Alkoxides – Cyano – Sterically hindered groups 13.4 Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

42 LAH is strong enough to also reduce esters and carboxylic acids, whereas NaBH 4 is generally not 13.4 Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

43 To reduce an ester, 2 hydride equivalents are needed 13.4 Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

44 To reduce an ester, 2 hydride equivalents are needed Which steps in the mechanism are reversible? 13.4 Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

45 Predict the products for the following processes Practice with SkillBuilder Alcohol Prep via Reduction Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

46 Diols are named using the same method as alcohols, except the suffix, “diol” is used 13.5 Preparation of Diols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

47 If two carbonyl groups are present, and enough moles of reducing agent are added, both can be reduced 13.5 Preparation of Diols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

48 Recall the methods we discussed in chapter 9 to convert an alkene into a diol 13.5 Preparation of Diols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

49 Grignard reagents are often used in the synthesis of alcohols To form a Grignard, an alkyl halide is treated with Mg metal How does the oxidation state of the carbon change upon forming the Grignard? 13.6 Grignard Reactions Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

50 The electronegativity difference between C (2.5) and Mg (1.3) is great enough that the bond has significant ionic character The carbon atom is not able to effectively stabilize the negative charge it carries Will it act as an acid, base, electrophile, nucleophile, etc.? 13.6 Grignard Reactions Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

51 If the Grignard reagent reacts with a carbonyl compound, an alcohol can result Note the similarities between the Grignard and LAH mechanisms 13.6 Grignard Reactions Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

52 Because the Grignard is both a strong base and a strong nucleophile, care must be taken to protect it from exposure to water If water can’t be used as the solvent, what solvent is appropriate? What techniques are used to keep atmospheric moisture out of the reaction? 13.6 Grignard Reactions Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

53 Grignard examples With an ester substrate, excess Grignard reagent is required. WHY? Propose a mechanism List some functional groups that are NOT compatible with the Grignard Practice with SkillBuilder Grignard Reactions Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

54 Design a synthesis for the following molecules starting from an alkyl halide and a carbonyl, each having 5 carbons or less 13.6 Grignard Reactions Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

55 Consider the reaction below. WHY won’t it work? The alcohol can act as an acid, especially in the presence of reactive reagents like the Grignard reagent The alcohol can be protected to prevent it from reacting 13.7 Protection of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

56 A three-step process is required to achieve the desired overall synthesis 13.7 Protection of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

57 One such protecting group is trimethylsilyl (TMS) The TMS protection step requires the presence of a base. Propose a mechanism 13.7 Protection of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

58 Evidence suggests that substitution at the Si atom occurs by an S N 2 mechanism Because Si is much larger than C, it is more open to backside attack 13.7 Protection of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

59 The TMS group can later be removed with H 3 O + or F - TBAF is often used to supply fluoride ions 13.7 Protection of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

60 13.7 Protection of Alcohols Practice with conceptual checkpoint Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

61 2 million tons of phenol is produced industrially yearly Acetone is a useful byproduct Phenol is a precursor in many chemical syntheses – Pharmaceuticals – Polymers – Adhesives – Food preservatives, etc Preparation of Phenols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

62 Recall this S N 1 reaction from section 7.5 For primary alcohols, the reaction occurs by an S N Reactions of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

63 The S N 2 reaction also occurs with ZnCl 2 as the reagent Recall from section 7.8 that the –OH group can be converted into a better leaving groups such as a tosyl group 13.9 Reactions of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

64 SOCl 2 can also be used to convert an alcohol to an alkyl chloride 13.9 Reactions of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

65 PBr 3 can also be used to convert an alcohol to an alkyl bromide Note that the last step of the SOCl 2 and PBr 3 mechanisms are S N 2 Practice with SkillBuilder Reactions of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

66 Fill in the necessary reagents for the conversions below 13.9 Reactions of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

67 In section 8.9, we saw that an acid (with a non- nucleophilic conjugate base) can promote E1 Why is E2 unlikely? Recall that the reaction generally produces the more substituted alkene product 13.9 E1 and E2 Reactions of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

68 If the alcohol is converted into a better leaving group, then a strong base can be used to promote E2 E2 reactions do not involve rearrangements. WHY? When applicable, E2 reactions also produce the more substituted product Practice with conceptual checkpoint E1 and E2 Reactions of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

69 We saw how alcohols can be formed by the reduction of a carbonyl The reverse process is also possible with the right reagents Oxidation of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

70 Oxidation of primary alcohols proceed to an aldehyde and subsequently to the carboxylic acid – Very few oxidizing reagents will stop at the aldehyde Oxidation of secondary alcohols produces a ketone – Very few agents are capable of oxidizing the ketone Oxidation of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

71 Tertiary alcohols generally do not undergo oxidation. WHY? There are two main methods to produce the most common oxidizing agent, chromic acid Oxidation of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

72 When chromic acid reacts with an alcohol, there are two main steps Oxidation of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

73 Chromic acid will generally oxidize a primary alcohol to a carboxylic acid PCC (pyridinium chlorochromate) can be used to stop at the aldehyde Oxidation of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

74 PCC (pyridinium chlorochromate) is generally used with methylene chloride as the solvent Both oxidizing agents will work with secondary alcohols Oxidation of Alcohols Practice with SkillBuilder 13.7 Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

75 Predict the product for the following reaction Oxidation of Alcohols Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

76 Nature employs reducing and oxidizing agents They are generally complex and selective. WHY? NADH is one such reducing agent Biological Redox Reactions Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

77 The reactive site of NADH acts as a hydride delivery agent This is one way nature converts carbonyls into alcohols Why is an enzyme required? Biological Redox Reactions Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

78 NAD + can undergo the reverse process The NADH / NAD + interconversion plays a big role in metabolism Biological Redox Reactions Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

79 Recall that tertiary alcohols do not undergo oxidation, because they lack an alpha proton You might expect phenol to be similarly unreactive Yet, phenol is even more readily oxidized than primary or secondary alcohols Oxidation of Phenol Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

80 Phenol oxidizes to form benzoquinone, which in turn can be reduced to hydroquinone Quinones are found everywhere in nature They are ubiquitous Oxidation of Phenol Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

81 Ubiquinones act to catalyze the conversion of oxygen into water, a key step in cellular respiration Where in a cell do you think unbiquinones are most likely found? Oxidation of Phenol Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

82 Ubiquinone catalysis: Oxidation of Phenol Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

83 Recall some functional group conversions we learned Synthetic Strategies Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

84 Classify the functional groups based on oxidation state Synthetic Strategies Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

85 13.13 Synthetic Strategies Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

86 13.13 Synthetic Strategies Give necessary reagents for the following conversions Practice with SkillBuilder 13.8 Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

87 13.13 Synthetic Strategies Recall the C-C bond forming reactions we learned Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

88 13.13 Synthetic Strategies What if you want to convert an aldehyde into a ketone? What reagents are needed for the following conversion? Practice with conceptual checkpoint and SkillBuilder 13.9 Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

89 Additional Practice Problems Name the following molecule Draw (1R,2R)-1-(3,3-dimethylbutyl)-3,5-cyclohexadien- 1,2-diol Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

90 Use ARIO and solvation to rank the following molecules in order of increasing pK a Additional Practice Problems Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

91 Predict the products for the following processes Additional Practice Problems Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

92 Design a synthesis for the following molecule starting from an alkyl halide and a carbonyl, each having 5 carbons or less Additional Practice Problems Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e

93 Give necessary reagents for the multi-step synthesis below Additional Practice Problems Copyright © 2015 John Wiley & Sons, Inc. All rights reserved Klein, Organic Chemistry 2e


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